Every Woody Harrelson Villain Role, Ranked

Summary

• Harrelson shines in his villainous roles, bringing depth to irredeemable characters and making audiences like them.
• He excels in morally ambiguous roles like True Detective’s detective with a dark side, showcasing his versatility as an actor.
• Harrelson’s captivating performances in movies like Venom and Natural Born Killers leave a lasting impact on viewers.

Woody Harrelson might have gotten his start on the beloved sitcom Cheers, but he soon transitioned to film and never looked back. During his long career starring in movies, Harrelson has been part of many projects, and while his performance remains believable no matter the character, he shines in his villainous roles. When he first began taking on characters that painted him in a darker light, it was a surprise to many audience members. However, he soon proved that not only could he bring depth to irredeemable people, he could make audiences like them.

It’s in these roles that operate in gray areas that Harrelson is best, but he can be just as compelling as a cold-hearted antagonist with no regard for the other characters.

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In the past few years, Harrelson made his mark in True Detective season 1, in which his character is a morally ambiguous detective who spends years tracking down a notorious killer. It’s in these roles that operate in gray areas that Harrelson is best, but he can be just as compelling as a cold-hearted antagonist with no regard for the other characters. Most of his villainous roles are in movies that have a central message that argues against violence and comments on how the media perpetuates crime and cruelty in its onscreen depictions.

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Celebrated for his larger-than-life characters, Woody Harrelson’s career in Hollywood has seen him in Oscar-winning movies and sidesplitting comedies.

8 Leland Powell – She Hate Me (2004)

Directed by Spike Lee

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In one of Spike Lee’s lesser-known movies, Harrelson plays a small but vile role as Leland Powell. Harrelson is far from the only heavy-hitter in the cast, as Anthony Mackie and Kerry Washington both star in the dramedy. Though Harrelson’s screen time is limited and his actions aren’t central to the plot’s main themes, Leland is pivotal in the inciting incident in the film. Additionally, Leland’s blatant greed and racism make him an obvious target for vitriol and allow the viewer to completely side with Jack (Mackie).

He and Mackie play off each other well in the few scenes they share, and Harrelson gives his all to the performance of a man willing to slander others to get what he wants.

The premise of the film caused controversy at the time, as its depictions of corporate America and the LGBTG+ community both came under fire. However, the purpose of Harrelson’s character doesn’t stir up discussion, as he’s the stand-in for the rampant prejudice and corruption that defines corporations. He and Mackie play off each other well in the few scenes they share, and Harrelson gives his all to the performance of a man willing to slander others to get what he wants.

7 Tobias Beckett – Solo: A Star Wars Story (2018)

Directed by Ron Howard

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Though Solo: A Star Wars Story is Star Wars‘ biggest box office bomb, there are some redeeming aspects of the prequel film, and Harrelson is one of them. In his role as Tobias Beckett, Harrelson is nearly as charming and slippery as Harrison Ford himself as the original Han Solo. It’s easy to be wary of Beckett throughout the story since he first appears as a criminal and nearly has Han killed, but, like any good villain, he slowly wins over Han and the audience. His final betrayal might have been obvious, but it still hits home.

Solo: A Star Wars Story might have been better received by critics and audiences if it had given even more screentime to Harrelson, who’s a more fleshed-out character than the young Han. Though Han is supposed to be a young man still figuring out where his loyalties lie, he doesn’t have the heroism or roguish nature that defines Ford’s iteration of the character. This makes it easy to root for Beckett over Han, even though the film is Han’s origin story.

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Solo: A Star Wars Story is a spin-off of the Star Wars franchise that focuses on the early years of Han Solo, with Alden Ehrenreich replacing Harrison Ford as the iconic smuggler. The movie explores how Han met Chewbacca, acquired the Millennium Falcon, and became the roguish smuggler fans know and love. Donald Glover brings back Lando Calrissian, Woody Harrelson plays Tobias Beckett, Emilia Clarke portrays Qi’ra, and Paul Bettany embodies the crime lord Dryden Vos.

Director Ron Howard Release Date May 10, 2018 Studio(s) Disney Cast Alden Ehrenreich , Emilia Clarke , Donald Glover , Woody Harrelson , Phoebe Waller-Bridge , Thandiwe Newton Runtime 135minutes Franchise(s) Star Wars Expand

6 Cletus Kasady/Carnage – Venom: Let There Be Carnage (2021)

Directed by Andy Serkis

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Though Harrelson briefly appears at the end of the first
Venom
movie as Cletus, he plays a much larger part in the sequel,
Venom: Let There Be Carnage
.

When Harrelson joins a larger franchise like Star Wars or Spider-Man, it’s usually in an off-beat or villainous role, like Carnage in the Venom movies. Though Harrelson briefly appears at the end of the first Venom movie as Cletus, he plays a much larger part in the sequel, Venom: Let There Be Carnage. When playing a comic book villain, the actor must be believably terrifying while incorporating the larger-than-life aspects of the character into the performance.

Unfortunately, Harrelson will likely not appear as part of the Venom: The Last Dance cast, as Venom defeated Carnage during the sequel. However, he’s set the bar high for the next villain in the franchise, as his chemistry with Venom actor Tom Hardy contributed to the success of the film. Unlike other antagonists in the Spider-Man universe, Carnage gets to push the boundaries of the story and his character, thanks to the darker tone and more violent elements of the movie. Harrelson also contributed much as the voice of Carnage and showed how adaptable his skills are for computer-generated characters.

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In this follow up to 2018’s Venom, Tom Hardy returns as the lethal protector Venom, an alien symbiote bonded to Eddie Brock. When Eddie gets a chance to interview one of the most dangerous serial killers on Earth, Cletus Kasady, an altercation between Kasady and Brock. This leads to the former getting his own parasite, and his twisted perception of the world gives life to Carnage, a deadly symbiote hellbent on chaos and death. Brock and Venom will have to work together to stop Kasady and Carnage’s murderous rampage.

Release Date October 1, 2021 Studio(s) Sony Cast Woody Harrelson , Peggy Lu , Michelle Williams , Reid Scott , Laurence Spellman , Stephen Graham , Tom Hardy , Amber Sienna , Naomie Harris , Sean Delaney Runtime 97 minutes Franchise(s) Venom

5 Dave Brown – Rampart (2011)

Directed by Oren Moverman

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Sigourney Weaver stars alongside Harrelson in Rampart, a crime film about a corrupt police officer, Dave Brown, who Harrelson embodies with a dangerous edge. The film’s story takes place in the wake of the Rampart scandal, which called for an investigation into the behavior and brutality of the LAPD, and Brown becomes the focus of the department’s issues as his legal battle commences. There’s little that redeems Brown in Rampart​​​​​​, making him more than just an anti-hero and propelling him into the role of full-blown villain. Every action pushes him further away from being any version of a good man.

It can be emotionally taxing to watch Rampart, as even though Brown faces an investigation into his behavior, he rarely experiences true consequences for his actions. The film takes a harsh look at the bureaucratic system that allows the continuation of police brutality, and it doesn’t provide the viewer with a happy ending. As Dave Brown, Harrelson is the center of the movie, and every part of the story hinges on his successful performance. Without Harrelson leading the cast, Rampart would be one-dimensional, but Harrelson gives it an edge.

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Rampart, directed by Oren Moverman, stars Woody Harrelson as veteran police officer Dave Brown in 1999 Los Angeles. The film follows Brown as he battles personal and professional turmoil while the LAPD Rampart scandal unfolds. Harrelson’s portrayal is complemented by strong performances from a supporting cast that includes Robin Wright, Sigourney Weaver, and Ice Cube. Rampart explores themes of corruption, morality, and redemption.

Director Oren Moverman Release Date November 23, 2011 Cast Sigourney Weaver , Woody Harrelson , Robin Wright , Steve Buscemi , Ben Foster , Brie Larson Runtime 108 Minutes

4 Harlan DeGroat – Out Of The Furnace (2013)

Directed by Scott Cooper

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Though
Out of the Furnace
was a box office bomb, it holds value in the skilled performances, if nothing else.

As the leader of a dangerous criminal ring, Harlan DeGroat, Harrelson holds his own against the strong performances of Christian Bale, Casey Affleck, and Willem Dafoe in Out of the Furnace. Though Out of the Furnace was a box office bomb, it holds value in the skilled performances, if nothing else. Though there was some controversy surrounding the film, it’s interesting to see Harrelson on the other side of the law, as he has portrayed law enforcement officers many times throughout his career.

In Out of the Furnace, Harrelson plays a drug dealer with a murderous streak, and the principal conflict comes down to his and Bale’s character, Russell. Overall, Out of the Furnace is more Bale’s movie than any other member of the cast, but without Harrelson, Bale’s character would have no reason to embark on his journey to help his brother. Harrelson cuts a striking and terrifying figure as DeGroat. The control he maintains with only the threat of violence and the men he employs demonstrates the importance of his character in the story.

Out of the Furnace tv-maThrillerDrama

Directed by Scott Cooper, Out of the Furnace is a 2013 Crime Drama featuring a star-studded cast that includes names like Christian Bale, Zoë Saldana, Forest Whitaker, Willem Dafoe, Woody Harrelson, and Casey Affleck. The plot sees two brothers struggle to adapt to civilian life and end up falling to a life of crime.

Director Scott Cooper Release Date December 6, 2013 Cast Christian Bale , Casey Affleck , Woody Harrelson , Zoe Saldana Runtime 116minutes

3 Colonel McCullough – War For The Planet Of The Apes (2017)

Directed by Matt Reeves

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The new Planet of the Apes movies are some of the best sci-fi and action dramas of the 21st century, and Harrelson’s sinister turn as Colonel McCullough is an example of what makes them so strong. None of the Planet of the Apes films rely on graphics or gimmicks to tell the story, instead opting for strong character development and interpersonal conflict to drive the narrative forward. War for the Planet of the Apes sees some of humanity’s worst moments as the conflict between humans and apes reaches its deadliest hour.

The Colonel is a large part of this escalation and is a stand-in for the most ruthless and violent impulses that humanity is capable of. War For the Planet of the Apes was a smash both critically and at the box office, and this wasn’t simply because of the excellent visual effects and well-choreographed action sequences. It takes a lot for a character to turn the audience against humanity, as this is the side viewers are used to rooting for, but Harrelson makes it easy to hate the forces he commands.

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War for the Planet of the Apes is an action-adventure movie directed by Matt Reeves and is a sequel to Dawn of the Planet of the Apes. In the film, Caesar and his apes are forced into a deadly conflict with an army of humans led by a ruthless colonel. After the apes suffer unimaginable losses, Caesar wrestles with his darker instincts and begins his mythic quest to avenge his kind.

Director Matt Reeves Release Date July 14, 2017 Studio(s) TSG Entertainment , Chernin Entertainment Cast Judy Greer , Steve Zahn , Mercedes de la Zerda , Max Lloyd-Jones , Woody Harrelson , Alessandro Juliani , Amiah Miller , Terry Notary , Andy Serkis , Aleks Paunovic , Ty Olsson , Devyn Dalton , Gabriel Chavarria Runtime 140 Minutes Franchise(s) Planet of the Apes prequel(s) dawn of the Planet of the apes movie , Rise of the Planet of the Apes , Planet of the Apes Expand

2 Charles Costello – Seven Psychopaths (2012)

Directed by Martin McDonagh

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Harrelson plays the gangster Charlie Costello, who makes trouble for the central trio, played by Sam Rockwell, Colin Farrell, and Christopher Walken.

Seven Psychopaths is a movie for movie lovers, as the primary thrust of the film is that the protagonist, Marty, is out of ideas for his screenplay. The film is in conversation with classic Los Angeles crime films and satires of the past and pokes fun at the Hollywood tropes and pitfalls that populate many thrillers. Harrelson plays the gangster Charlie Costello, who makes trouble for the central trio, played by Sam Rockwell, Colin Farrell, and Christopher Walken.

Seven Psychopaths was perfect for Harrelson because he got to demonstrate not only his dramatic and intimidating side but also his comedic skills and timing. The irony and self-awareness with which Harrelson plays Costello demonstrates what critics and audiences appreciate about Seven Psychopaths, as the balance between outlandish humor and startling violence finds tonal balance in the narrative. Like many movies that Harrelson has starred in, Seven Psychopaths questions the use and graphic nature of violence in cinema,] and how it affects people’s perceptions of tragedy.

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Seven Psychopaths follows a writer with a major block named Marty looking to create his next big screenplay, only knowing that he has the title for the film set in stone. Joined by his two friends who kidnap dogs from the wealthy to make ransom money, his greatest story yet may have the content it needs when the pair of dog nappers accidentally kidnap a gangster’s dog, leading to a desert showdown rife with violence and dark comedy. 

Director Martin McDonagh Release Date October 12, 2012 Studio(s) Film4 , HanWay Films , Blueprint Pictures , BFI Cast Colin Farrell , Sam Rockwell , Woody Harrelson , Christopher Walken , Tom Waits , Abbie Cornish , Olga Kurylenko Runtime 110 Minutes

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1 Mickey Knox – Natural Born Killers (1994)

Directed by William Oliver Stone

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In one of his best roles ever, Harrelson is one of many villains in Natural Born Killers, the film that has generated controversy and intense debate over its violent themes. However, even as Harrelson’s Mickey Knox commits some of the worst crimes imaginable, it’s not just him that the movie implicates, but society as a whole. Natural Born Killers looks at the intersection between cycles of abuse perpetuating violence and how the media feeds off of these sensationalized stories about desperate people in terrible situations. In the end, Natural Born Killers doesn’t absolve Mickey; it condemns the viewer alongside him.

It will be interesting to see Harrelson’s new movie that flips his role in Natural Born Killers. Lips Like Sugar will see him team up with Owen Wilson as detectives. Woody Harrelson was still relatively early in his career when he took on the role of Mickey, and his performance in the film changed the way audiences and filmmakers viewed him forever. Even in 1994, after primarily starring in comedies, the actor had a depth and darkness to him that couldn’t be faked. Without his portrayal of Mickey, Natural Born Killers would not be as well-remembered today.

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The 1994 crime thriller Natural Born Killers, adapted from an original story by Quentin Tarantino and directed by Oliver Stone, tells the story of two murderers who become celebrities due to their charming personality. Woody Harrelson and Juliette Lewis star as criminals Mickey and Mallory Knox, with Robert Downey Jr. as sleazy journalist Wayne Gale, Tom Sizemore as Detective Jack Scagnetti, and Tommy Lee Jones as Warden Dwight McClusky.

Director Oliver Stone Release Date August 26, 1994 Studio(s) Warner Bros. Pictures Cast Robert Downey Jr. , Juliette Lewis , Tom Sizemore , Woody Harrelson , Rodney Dangerfield Runtime 118 minutes

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Category: Entertainment